Every year I deposit the max to my HSA with the 1000 catch-up along with 1000 catch-up to my wife’s account. I dont spend any of this and categorize all my medical expenses appropriately. I am trying to figure out how I put the HSA deposits in my HSA accounts. I put transfer from my brokerage account but that doesn’t track it. How does everyone do it? It is clearly not income or an expense so I am open to your thoughts. Thanks, Jim
What info do you want to track and how do you want it presented (what template)?
Having the HSA account linked to Tiller is tracking the HSA balance.
The Transactions sheet has the transfers, so you can filter the data to see them, or create your own sheet with a formula or pivot table that always lists the HSA transfers.
I do think categorizing it as a Transfer is correct, since it is a transfer between accounts.
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I do the same but with a high yield savings account which I don’t have linked. I track on a separate Excel tab. I categorize the outbound deposit as a transfer. I think the concept is the same.
I also use the Transfer category for HSA contributions. Our HSA accounts are linked to Tiller.
We are also “saving” our medical expenses for later year HSA withdrawals. In the year that we have the expense, I use the appropriate category for the expenses and add a Tag called HSA Eligible.
Our HSA records are older than when we started using Tiller, so I have a separate spreadsheet where I am tracking all of these HSA items - annual contributions, annual inv gain/loss, eligible expenses, and verification that the various receipts have been loaded to my cloud storage into a folder called HSA Future Claims with subfolders by year. I use the Tiller “Tags Report” to keep my records in sync.
In 2025, we made our first HSA withdrawals. I again used the Transfer category to move money between the accounts. For the amount coming OUT of the HSA, I added a Tag called HSA Paid. I updated my separate spreadsheet with the withdrawal date/amount and verification that I have moved my receipt documentation in cloud storage from HSA Future Claims to HSA Paid Claims, again with yearly subfolders.
I have a Pivot Table within Tiller for the HSA Paid tags that should match up to the 1099 that gets issued.
It’s a lot of documentation to maintain, but for the tax-free money, it’s worth doing. I try to do all the HSA scanning and cloud storage file movement quarterly.
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